Trip ideas for the Keys in June

We're planning a two week trip in early June to the keys. We'll likely fly into Miami and rent a car. I grew up in south Florida but haven't been back since I was a teenager. I have very fond memories of floating around with my snorkel and mask on, checking out fish, fishing, and wandering the beach at low tide looking at creatures in tide pools and rock pools. My 7 year old daughter loves these things, but hasn't had a chance to do snorkeling in the ocean yet. I'm thinking of just setting up base camp on Key Largo and doing the glass bottom boat tour, maybe one day of a chartered private fishing boat, a day of eco tourism kayaking in the everglades, and all the time in-between spent at the beach at John Pennekamp snorkeling, swimming, and looking for water creatures. It'll be me, my wife, and our 7 and 5 year old daughters.

Anybody have any further suggestions or critiques of my agenda ideas? Any locals have suggestions on specific fishing or tour companies? Anybody think a different key would be better?

I initially thought of a driving trip stopping at a bunch of different places, but my wife's idea of a vacation is to go somewhere and stay for a while to really unwind. Too much sitting and driving is not conducive to relaxing for her. That sounds good to me, too, so flying or a quick dash to get there it is. We're about 18 hours of driving from Key Largo, so it's likely we'll fly.

My wife and I just spent a week there in October for our honeymoon (you may or may not know I got divorced a few years back and just remarried).  We had never been to the Keys, so we wanted to see as much as we could.  We stayed roughly in the middle on Key Colony Beach.  It's a tiny island right outside of Marathon.  That way it was only an hour drive to Key Largo or Key West.  We had a fabulous time.  I'm not a fishing person, so we didn't do that.  However we did take a snorkeling trip and sunset cruise (I think your daughters would be allowed too, pretty sure there were kids on our boat).  The snorkeling trip was through Fury Watersports.  It was great.  The crew was super helpful and cared about their jobs.  Our sunset cruise was on this boat... https://schoonerjollyrover.com/   Really enjoyed them too, the captain was fantastic.  

I know you were looking at Key Largo.  Sorry I don't have a lot of suggestions there, as we didn't spend much time on the north end.  We did really enjoy being in the middle though, easy access to anywhere in the Keys.  Our resort was great too.

Good Karma Sportfishing out of Islamorada was the most fun I've ever had fishing in my life.  He put us on the fish so hard, it was amazing! 

https://goodkarmasportfishing.com/

If you are ah...free spirited? you could visit the Garden of Eden bar in KeyWest.

I'd look into the shuttle bus to key West. It's a much nicer ride than drive. It's great scenery, so enjoy it and let someone else have the headache. We fly into Marathon, and stay on Duck, so it's a little closer to Key West, but makes a nice day trip. 

My lady and I will be down there in April (Elton John concert in Miami) so I'm following this thread for suggestions. We are going to stay in Marathon ourselves. We will have a car, and our own snorkeling gear at least while down there.

Any restaurant recommendations would be greatly appreciated, I'd put us under the 'foodie' label and don't mind spending money on a good meal, we do plan on visiting key west at least once.

For the foodies:

Key West:

• FireFly (Southern food)
• Santiago's Bodega (Tapas)
• Amigos Tortilla Bar (excellent tacos)
• Onlywood (Pizza/Italian - The one right off of Duval street)
• Tiger Bar (order the whole menu, believe me)
• Seven Fish
• La Grignote (Breakfast)

Islamorada:

• Shrimp Shack

Key Largo:

• The Fish House

Marathon:

• Herbie's

The best ones are in Key West, but fish is always good and fresh in the keys. If you want me to expand to Miami, let me know.

Try and go to Tortugas if you can, whole day trip is best. Not sure now with the covid thing, but you had to book the trip in advance. Bring a snorkel and mask.

Awesome input so far! I'm just about to nail it down and buy plane tickets and lodging. I'll update here when we do. Thanks guys.

There is a pinecrest bakery in islamorada- highly suggested the guava pastry. Also would suggest dinner at Pierre's on the deck near sunset. It's insane. They have a great ahi tuna steak. 
glazed donuts and coffee in key west is a staple for us. Also a great taco shop that I can't recall the name of right now. 
The keys are an interesting place but your best bet is key west or rent a house in islamorada. 

In reply to Slippery :

For me personally, having options in Miami would be excellent, we are going to be there for 2 days as well. We already booked dinners, and a tour around little havana, but otherwise are open. We are going to stay in South Beach while we are there.

Heading out in the morning! We rented a jeep through Turo we'll see how that goes. 

SUNSCREEN or hats are a must. 

The snorkel trips out of Pennekamp in Key Largo are easy access to shallow, nice reefs. I've heard similar about Looe Key further south but never gone there myself.  The boats tend to have a lot of people on them so when Ive done that I like to spread out and swim further away. 

Also recommend going to Fort Jefferson - it's a full day in the ferry, or fly on float planes. I've taken my boat a few times. Decent snorkeling by the fort (awesome snorkeling if you go by your own boat), and the architecture and history are pretty cool. 

Blue Heaven for a cool breakfast/brunch experience on Key West

Mel Fisher museum is cool, but don't know how much fun it would be for a 7 year old, but maybe. Duval Street/Mallory Square in the late afternoon/evening is fun to see with the street vendors and performers. Good food too, try the conch fritters. 
 

As mentioned, Blue Heaven is a great breakfast spot and the young ones will like all of the chickens running around.

So, bumping this because I realized I never provided a trip report.. the trip went ... ok. We got there and had a fun first day, running down to Robbie's on Islamorada and feeding the tarpon and playing on the beach chasing hermit crabs and snorkeling. Then I started to feel sick, and then sicker, and then the next morning tested positive for Covid. yay. Glass bottom boat ride, cancelled. Fishing charter, out of the question. Restaurants, nope. We made the best of it, doing some amazing shore fishing and my 7 year old (now 8!) caught a bunch of grouper, grunts, snapper, etc. I caught a 4' or 5' nurse shark from the fishing pier of the condo we were staying at.

We discovered an amazing park in walking distance from our condo on Key Largo called Rowell's Waterfront Park. It was rough and in bad repair but it was a former marina and the marina area makes for an incredible swimming/snorkeling hole since it's so deep. We got to swim with tarpon, barracuda, and check out coral and starfish and catch gobies, barracuda, and gar. It was great, and we walked down there several times.

My wife and 5 year old got Covid (amazingly enough the 7 year old never did) and my wife got an ear infection that was bad enough the urgent care in the keys told her she shouldn't fly. So we did a one-way rental and drove back. That actually went really well, we stopped at ichetucknee springs and tubed down the river, twice. We stopped at my cousin's new farm in TN, we had a blast.

BUT, amazingly enough the airline gave us a big enough credit for not making the return trip that we got a free flight for the four of us to the Keys in February. We leave in a couple weeks and I've got a place on Marathon lined up. I'm thinking about renting a boat for the week, any advice on that? Looks like about $1000 after taxes gets us a 22' Boston Whaler, we can leave it at their dock and go get it as desired. It's a lot of money but opens up a lot of recreation to have our own transportation on the water for the week.

I'll try to get to some of the fun stuff mentioned here, hopefully we don't get Covid this time and can enjoy things that involve being around other people.

grover said:

There is a pinecrest bakery in islamorada- highly suggested the guava pastry.

We did end up going to Pinecrest several times. I could not get enough of the guava pastry it was excellent. THANK YOU for the suggestion.

We discovered an awesome and brand new food truck on Key Largo called Tartares de Rebeca. It was a mother and son pair running the place and they had opened only a month or so previously. Probably the best fish sandwich I've ever had in my life, and amazing fruit smoothies, and super nice people. They were just so genuine and lovely and we ate there three or four times and enjoyed everything we tried, but the snapper sandwich was the best.

We ate at an absolute hole in the wall cuban place on Islamorada (or was it Marathon?) whose name I forget. Looked like a shack, right out on the Overseas Highway. It was $7 for an absolutely amazing sandwich. I love tortas and they had really good ones. We got four sandwiches for the four of us and finished maybe 1.5 of them. The rest we kept in the fridge and ate the next day, still good. We'll find the place again and post up about it. Since we're closer I'm sure it'll be a staple this time.

NMVA:  

https://keywestcoastalcharters.com/

This Captain is a friend of ours.  Very professional and very knowledgable.  

In reply to GeddesB :

Looks like a great option; what's your name so I can let her know how we found out about her? (Assuming it works out!)

Damn now you have me checking for a family spring break trip.  We spent a day in the Keys on our Honeymoon Cruise a million years ago and I'm dying to get back and see it with the family.  Sadly my first pass says my hotel points aren't rich enough.  Apparently 80-100K points per night for the nicer stuff in key west.  Marathon wasn't much cheaper...  To be continued.

In reply to GeddesB :

Booked her for next week! I'm excited. I may skip the boat rental this time and will just do a charter or two. I don't have any experience operating on open water and am a little nervous about it. 

June? Sounds hot.

In reply to dculberson :

A legit local charter guy will have the fish jumping into your boat.  I always target the first day or two of the trip so we can have fresh fish dinner.  Kiddos are great out for lunch but by dinner after a day at the beach they are toast.  Some of the best times my bro's and Dad had were a last minute charter.

In reply to dculberson :

Tell her Bill and Michelle said Hi!!

Datsun310Guy said:

June? Sounds hot.

June was the last trip and it was amazing. The keys don't get that hot, nor do they get that cold. It was 78 there today and when we were there in June it wasn't much warmer. 
 

this trip starts 7am tomorrow.

@GeddesB: will do!